ArticleACS medicinal chemistry letters2021
Cell Permeability of Isomeric Macrocycles: Predictions and NMR Studies.
Article in ACS medicinal chemistry letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
17 citing papers in PubMed.
- CalVSP: a program for analyzing the molecular surface areas, volumes, and polar surface areas.Journal of cheminformatics · 2025Article
- Backbone Alterations in Cyclic Peptides Influence Both Membrane Permeability and Biological Activity.Journal of medicinal chemistry · 2025Article
- Exploring Macrocyclic Chemical Space: Strategies and Technologies for Drug Discovery.Pharmaceuticals (Basel, Switzerland) · 2025Review
- Conservation of structure and dynamic behavior in triazine macrocycles with opportunities for subtle control of hinge motion.Organic & biomolecular chemistry · 2025Article
- A membrane permeability database for nonpeptidic macrocycles.Scientific data · 2025Article
- Validating Small-Molecule Force Fields for Macrocyclic Compounds Using NMR Data in Different Solvents.Journal of chemical information and modeling · 2024Article
- Cell penetration of oxadiazole-containing macrocycles.RSC chemical biology · 2024Article
- Membrane Permeability in a Large Macrocyclic Peptide Driven by a Saddle-Shaped Conformation.Journal of the American Chemical Society · 2024Article
- Addressing Challenges of Macrocyclic Conformational Sampling in Polar and Apolar Solvents: Lessons for Chameleonicity.Journal of chemical information and modeling · 2023Article
- Adaptation of Empirical Methods to Predict the LogD of Triazine Macrocycles.ACS medicinal chemistry letters · 2023Article
- Controlling the Evolution of Selective Vancomycin Resistance through Successful Ophthalmic Eye-Drop Preparation of Vancomycin-Loaded Nanoliposomes Using the Active-Loading Method.Pharmaceutics · 2023Article
- Isolation and NMR Scaling Factors for the Structure Determination of Lobatolide H, a Flexible Sesquiterpene fromInternational journal of molecular sciences · 2023Article
- Going Viral: An Investigation into the Chameleonic Behaviour of Antiviral Compounds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- A story of peptides, lipophilicity and chromatography - back and forth in time.RSC medicinal chemistry · 2022Review
- Hydrocarbon Macrocycle Conformer Ensembles andAngewandte Chemie (International ed. in English) · 2022Article
- A New Amino Acid for Improving Permeability and Solubility in Macrocyclic Peptides through Side Chain-to-Backbone Hydrogen Bonding.Journal of medicinal chemistry · 2022Article
- Pushing the Limits of Characterising a Weak Halogen Bond in Solution.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Conformation-dependent 3D descriptors have been shown to provide better predictions of the physicochemical properties of macrocycles than 2D descriptors. However, the computational identification of relevant conformations for macrocycles is nontrivial. Herein, we report that the Caco-2 cell permeability difference between a pair of diastereomeric macrocycles correlated with their solvent accessible 3D polar surface area and radius of gyration. The descriptors were calculated from the macrocycles' solution-phase conformational ensembles and independently from ensembles obtained by conformational sampling. Calculation of the two descriptors for three other stereo- and regioisomeric macrocycles also allowed the correct ranking of their cell permeability. Methods for conformational sampling may thus allow ranking of passive permeability for moderately flexible macrocycles, thereby contributing to the prioritization of macrocycles for synthesis in lead optimization.
Identifiers
What Socratic holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.